4'-Bromo-2,2,2-trifluoroacetophenone → 1-(4-Bromophenyl)-2,2,2-trifluoroethanol

4′-Bromo-2,2,2-trifluoroacetophenone (3.00 mL, 19.8 mmol) was stirred in MeOH (66 mL) at 0° C. Sodium borohydride (0.748 g, 19.8 mmol) was added and the mixture was allowed to warm to ambient temperature. The mixture was stirred for 3 hours, then quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was then washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by MPLC (eluting with 5% EtOAc/hexanes). Desired fractions were identified, combined, and concentrated in vacuo to afford a racemic mixture of the title compounds. The racemic residue was resolved by Chiral SFC purification (Chiral Technology OJ-H 2.1×25 cm, 5 uM Column; eluting with 5% isopropyl alcohol/CO2).

1. customquenched with saturated aqueous ammonium chloride
2. extractionextracted with ethyl acetate
3. washThe organic layer was then washed with brine
4. dry with materialdried over anhydrous MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified by MPLC (eluting with 5% EtOAc/hexanes)
8. concentrationconcentrated in vacuo
9. customto afford
10. customThe racemic residue was resolved by Chiral SFC purification (Chiral Technology OJ-H 2.1×25 cm, 5 uM Column; eluting with 5% isopropyl alcohol/CO2)

ORD record

ord-481e6e37636e46419f3e0bd6f542dad7

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962608B2